JPH1143406A - Herbicidal composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a herbicidal composition capable of selectively weeding weed in wide range, especially in soybean field by including a specific phenoxyacetic acid ester derivative and one kind of herbicide among imazethapyr, imazaquin and imazamox. SOLUTION: This herbicidal composition contains (A) 2-chloro-4-fluoro-5-(4- methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetic acid ester derivative and (B) one kind of herbicide selected from (±)-2-[4,5-dihydro-4-methyl-4-(1- methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3-pyridinecarboxylic acid, (±)-2-[4,5- dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinoline carboxylic acid and 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(methoxymethyl)nico tinic acid in a weight ratio of components A/B of 1/(0.5-50).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a herbicide composition, and more particularly to a herbicide composition for foliage treatment and a method for herbicide treatment by foliar application of the composition to weeds.

[0002]

2. Description of the Related Art At present, a large number of herbicides are commercially available and used. Therefore, there is a demand for safe herbicides in crops, which have a wide spectrum of herbicides and which have high cropping rates.

[0003]

The present inventors have conducted intensive studies to find an excellent herbicide, and as a result, have found that 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3).
-Pyridazinone-2-yl) phenoxyacetic acid ester derivative and (±) -2- [4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1H-imidazole-2. -Yl] -5-ethyl-3-pyridinecarboxylic acid (general name imazethapyr, hereinafter referred to as imazethapyr) or a salt thereof, (±) -2- [4,5-dihydro-4
-Methyl-4- (1-methylethyl) -5-oxo-1
H-Imidazol-2-yl] -3-quinolinecarboxylic acid (generic name imazaquin, hereinafter referred to as imazaquin) or a salt thereof and 2- (4-isopropyl-4-methyl-5-oxo-2-imidazoline-2) A foliar treatment of a weed with a herbicide composition containing, as an active ingredient, -yl) -5- (methoxymethyl) nicotinic acid (general name imazamox, hereinafter referred to as imazamox) or one selected from a salt thereof. By doing so, weeds can be effectively removed from a variety of weeds that occur on agricultural or non-agricultural lands, and the herbicidal efficacy increases synergistically compared to the case where they are used alone. It has been found that the herbicidal spectrum can be broadened, and that weeds can be selectively removed from a wide range of weeds, particularly in a soybean field, and the present invention has been achieved. That is, the present invention provides 2-chloro-4-fluoro-5- (4-methyl-5
-Trifluoromethyl-3-pyridazinone-2-yl)
A herbicidal composition for foliage treatment comprising a phenoxyacetic acid ester derivative and imazethapyr or a salt thereof, imazaquin or a salt thereof and one selected from the group consisting of imazamox or a salt thereof as active ingredients (hereinafter referred to as the present composition) ) And a method for foliar application of the same to weeds. Incidentally, the salt in the composition of the present invention means an agrochemically acceptable salt such as an alkali metal salt, an alkaline earth metal salt, an amine salt such as isopropylamine salt or an ammonium salt.

[0004]

DETAILED DESCRIPTION OF THE INVENTION 2-Chloro-4-fluoro-5- (4-methyl-5) which is one of the active ingredients of the composition of the present invention.
-Trifluoromethyl-3-pyridazinone-2-yl)
In the phenoxyacetic acid ester derivative, the ester means C1 to C7 alkyl ester, C5 to C6 cycloalkyl ester, and C2 to C6 alkenyl ester, and these compounds can be produced by the method shown in the following production examples. . Production Example 1 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone was added to a mixture of 5.3 g (53.3 mmol) of sodium acetate and about 100 ml of water under ice-cooling. 2 at ℃
Stirred for 0 minutes. The reaction was cooled to room temperature and
A solution of 5.8 g (21.5 mmol) of fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the mixture was stirred at room temperature for 1 hour. The ether layer was separated and concentrated, and about 60 ml of tetrahydrofuran (hereinafter referred to as "THF") was added to the residue, and 8.3 g (23.0 mm) of carbethoxyethylidenetriphenylphosphorane was added thereto.
ol) and heated to reflux for 2 hours. After the THF was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography.
To give 3.8 g (10.5 mmol) of 2- [2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one. 2
3.5 g (9.7 mmol) of-[2-fluoro-4-chloro-5-isopropoxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one was added under ice-cooling to about 10 m of concentrated sulfuric acid.
l and warmed to room temperature. After 10 minutes, about 1
00 ml of water was added, and the resulting crystals were collected by filtration and twice with 20 ml of water.
Washing was sequentially performed once with 10 ml of hexane. The obtained crystals were recrystallized from isopropanol to give 2- [2-fluoro-4
-Chloro-5-hydroxyphenyl] -4-methyl-5
3.2 g of trifluoromethylpyridazin-3-one (9.9 m
mol). 2- [2-fluoro-4-chloro-5-
Hydroxyphenyl] -4-methyl-5-trifluoromethylpyridazin-3-one 3.2 g (9.9 mmol) in DMF
Dissolve in about 50 ml and add sodium hydride (60 wt%
Add 0.44 g (11 mmol) of oil dispersion and add 30
After leaving at room temperature for 10 minutes, the mixture was cooled on ice, and ethyl bromoacetate (1.8 g, 11 g) was added.
mmol). After stirring at room temperature for 1 hour, diethyl ether and water were sequentially added and extracted. The organic layer was washed successively with a 10% aqueous hydrochloric acid solution, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography.
And ethyl 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetate (hereinafter referred to as compound A).
2.4 g (5.5 mmol) were obtained. Melting point 102.0 ° C

Production Example 2 The same procedure as in Production Example 1 was carried out except that the following reaction reagents were used instead of ethyl bromoacetate, whereby the desired 2-chloro-4-fluoro-5- ( 4
-Methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative can be obtained.

[Table 1] (In the table, i represents iso, t represents tertiary, and c represents cyclo.)

[0006] ¹ H-NMR (250 MHz or 300 MHz)
MHz, CDCl ₃ , TMS, δ (ppm)) Compound E 0.88 (3H, t, J = 7 Hz), 1.2-1.4
(4H, m), 1.55-1.70 (2H, m), 2.
43 (3H, q, J = 2 Hz), 4.19 (2H, t,
J = 7 Hz), 4.68 (2H, s), 6.98 (1
H, d, J = 7 Hz), 7.33 (1H, d, J = 8H)
z), 7.99 (1H, s) Compound H 1.26 (6H, d, J = 6.3 Hz), 2.43 (3
H, q, J = 2 Hz), 4.65 (2H, s), 5.0
5-5.18 (1H, m), 6.98 (1H, d, J =
7 Hz), 7.33 (1H, d, J = 8 Hz), 7.9
8 (1H, s) Compound I 0.90 (6H, d, J = 6.6 Hz), 1.85 −
2.03 (1H, m), 2.42 (3H, q, J = 1.
8 Hz), 3.98 (2H, d, J = 6.5 Hz),
4.70 (2H, s), 6.99 (1H, d, J = 6.
3Hz), 7.33 (1H, d, J = 9.1 Hz),
7.98 (1H, s) Compound J 1.45-1.53 (9H, m), 2.39-2.45
(3H, m), 4.58-4.60 (2H, m), 6.
96-7.00 (1H, m), 7.30-7.36 (1
H, m), 7.96-8.00 (1H, m) Compound K 1.5-1.9 (8H, m), 2.43 (3H, q, J
= 2 Hz), 4.65 (2H, s), 5.2-5.4
(1H, m), 6.97 (1H, d, J = 7 Hz),
7.33 (1H, d, J = 8 Hz), 7.98 (1H, d, J = 8 Hz)
s) Compound M 2.42 (3H, q, J = 1.9 Hz), 4.67-
4.72 (2H, m), 5.23-5.37 (2H,
m), 5.84-5.98 (1H, m), 7.00 (1
H, d, J = 6.3 Hz), 7.33 (1H, d, J =
9.2 Hz), 7.99 (1H, s) Compound N 2.42 (3H, q, J = 1.8 Hz), 4.68−
4.71 (1H, m), 4.77 (2H, s), 4.9
4-5.01 (1H, m), 7.03 (1H, d, J =
6.3 Hz), 7.26-7.31 (1H, m), 7.
34 (1H, d, J = 9.0 Hz), 7.99 (1H, d, J = 9.0 Hz)
s)

[0007] Imazethapyr is available from the Farm Chemicals Handbook.
, 1995 (Meister, Publishing Co., 199
5 years) Compound described on page C312. Imazakin
Farm Chemicals Handbook, 1995 (Meister, Publi
shing Co., 1995) C332. Imazamox is AG CHEM NEW COMPOUND REV
IEW, VOLUME 13,1995 (AG CHEM INFORMATION SERVI
CES, 1995), page 13.

The composition of the present invention provides an effective herbicidal composition for selectively controlling a wide range of weeds and for applying to new cultivation methods such as no-tillage cultivation. In particular, major weeds in soybean fields, such as buckwheat, Sanaetada, Sasaetada, Purslane, Shiroza, Aogetou, Noharagarashi, Tsunoxanem, Ebisugusa, Ichibi, American dragon deer, American morning glory, Malva morning glory, Malva American Dicotyledonous plants such as morning glory, artichoke mackerel, dogwood, onamimomi, sunflower, medaka, mulberry, euphorbia americana, ragweed, etc. Yatta - Ke - while effectively herbicidal monocotyledons such emissions, no phytotoxicity, such as a problem with respect to maize crop after soybeans and soybean crop.

In the composition of the present invention, 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester derivative as an active ingredient, imazethapyr or The mixture ratio of the salt, imazaquin or a salt thereof and one selected from the group consisting of imazamox or a salt thereof may vary depending on the target weed species, application scene, application conditions, and the like.
The weight ratio is usually in the range of 1: 0.5 to 50.

[0010] The composition of the present invention is usually mixed with a solid carrier, a liquid carrier and the like, and if necessary, added with a surfactant and other auxiliaries for formulation, etc., to form an emulsion, a wettable powder, a suspension and the like. It is used after conversion. In these formulations, 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-
The total amount of the 3-pyridazinone-2-yl) phenoxyacetic acid ester derivative and one selected from the group consisting of imazethapyr or a salt thereof, imazaquin or a salt thereof, and imazamox or a salt thereof is generally 0.5 to 90% by weight, preferably 0.5 to 90% by weight. Is contained in an amount of 1 to 80% by weight.

[0011] The solid carrier used in the preparation includes, for example, clays (kaolinite, diatomaceous earth, synthetic hydrous silicon oxide, fubasamikure, bentonite, acid clay, etc.), talc, and other inorganic minerals (sericite, quartz) Powder, sulfur powder, activated carbon, calcium carbonate, etc.) and fine powders and granular materials such as chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, salt ammonium salt, urea, etc.). Examples of the liquid carrier include water, alcohol and the like. (E.g., methanol, ethanol), ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, methylnaphthalene), non-aromatic hydrocarbons (e.g., hexane, cyclohexane) , Kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile) Le etc.), e - ethers (dioxane, diisopropyl et - ether, etc.), acid amides (dimethylformamide, dimethylacetamide), halogenated hydrocarbons (dichloroethane, trichlorethylene, etc.) and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, and polyethylene glycol ethers.
Examples include ters, polyhydric alcohol esters, and sugar alcohol derivatives. Other formulation aids include:
For example, fixing agents such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.). And dispersant, PAP (isopropyl isopropyl phosphate), BHT (2,6-tert-butyl-4-methylphenol), BHA (2- / 3-tert-butyl-
4-methoxyphenol), vegetable oil, mineral oil, fatty acid,
Stabilizers such as fatty acid esters are included.

The composition of the present invention can also be prepared by formulating each of the active ingredients by the above-mentioned formulation technique and then mixing them. The composition of the present invention thus formulated is applied to a plant as it is or diluted with water or the like. The composition of the present invention can further be expected to enhance herbicidal efficacy by being used in combination with other herbicides, and can also be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, soil improvers, and the like. it can.

The application rate of the composition of the present invention is as follows: 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2-yl) phenoxyacetic acid ester which is an active ingredient compound. Mixing ratio of the derivative with imazethapyr or a salt thereof, imazaquin or a salt thereof and one selected from the group consisting of imazamox or a salt thereof, weather conditions, formulation form, application time, application method, application place, weeds to be controlled, target Although it may vary depending on the crop, the total amount of the active ingredient compound per hectare is usually 5 to 500 g.
It is. Emulsions, wettable powders, suspensions and the like are applied by diluting a predetermined amount thereof with 100 to 1,000 liters of water per hectare.

[0015]

[Examples] Formulation examples are shown below. In the following examples, parts represent parts by weight. Formulation Example 1 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
Compound K, Compound L, Compound M or Compound N (10 parts), Imazethapyr or a salt thereof (35 parts), lignin sulfonate (3 parts), sodium lauryl sulfate (2 parts) and synthetic hydrous silicon oxide (50 parts) are thoroughly pulverized and mixed to obtain a wettable powder. . Formulation Example 2 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
Compound K, Compound L, Compound M or Compound N (10 parts), Imazaquin or its salt (35 parts), lignin sulfonate (3 parts), lauryl sulfate (2 parts) and synthetic hydrous silicon oxide (50 parts) are thoroughly pulverized and mixed to obtain a wettable powder. . Formulation Example 3 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
20 parts of compound K, compound L, compound M or compound N, 40 parts of imazamox or a salt thereof, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 35 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain a wettable powder. .

Formulation Example 4 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
5 parts of compound K, compound L, compound M or compound N, 20 parts of imazamox or a salt thereof, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 70 parts of synthetic silicon oxide hydroxide are thoroughly pulverized and mixed to obtain a wettable powder. . Formulation Example 5 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
10 parts of compound K, compound L, compound M or compound N, 35 parts of izetapyr or a salt thereof, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 49 parts of water were mixed, The suspension is obtained by wet grinding until the particle size is less than 5 microns. Formulation Example 6 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
10 parts of compound K, compound L, compound M or compound N, 35 parts of imazaquin or a salt thereof, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 49 parts of water, The suspension is obtained by wet grinding until the particle size is less than 5 microns.

Formulation Example 7 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
10 parts of compound K, compound L, compound M or compound N, 20 parts of imazamox or a salt thereof, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethyl cellulose) and 64 parts of water, Particle size is 5
The suspension is obtained by wet milling to submicron size. Formulation Example 8 Compound A, Compound B, Compound C, Compound D, Compound E,
Compound F, Compound G, Compound H, Compound I, Compound J,
5 parts of compound K, compound L, compound M or compound N, 10 parts of imazamox or a salt thereof, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 79 parts of water, The suspension is obtained by wet grinding until the particle size is less than 5 microns.

Hereinafter, test examples will be described. Evaluation criteria Herbicidal efficacy was evaluated as “0” when the emergence or growth of the test weed at the time of the survey showed no or little difference from that of the untreated one, and the test plant completely died or emerged or "10" indicates that growth is completely suppressed
And divided into 11 stages of 0 to 10, 0, 1, 2,
3, 4, 5, 6, 7, 8, 9, and 10. The evaluation values "7", "8", "9", and "10" of the herbicidal effect indicate excellent herbicidal effects, and the evaluation value "6" or less indicates insufficient herbicidal effect. Evaluation of phytotoxicity is `` harmless '' when little phytotoxicity is found, `` small '' when mild phytotoxicity is found, `` medium '' when moderate phytotoxicity is found, and `` harmless '' when severe phytotoxicity is found Indicated by "Large".

[0019] Test Example 1 area 26.5 × 19cm ^2, soybean filled with upland soil in a plastic pot of depth 7 cm, giant foxtail,
The crabgrass was sowed and grown in a greenhouse for 23 days. Compound E 10 parts, polyoxyethylene styryl phenyl ether 14 parts, calcium dodecylbenzenesulfonate 6
E, an imazethapyr formulation (Pursuit: manufactured by American Cyanamid Co.), and a mixture of the compound E emulsion and imazethapyr formulation obtained by thoroughly mixing 35 parts of xylene and 35 parts of cyclohexanone Were diluted with water and sprayed evenly from above the plants with a small sprayer. Grow in a greenhouse for 4 days after treatment,
Herbicidal efficacy and soybean safety were investigated. Table 2 shows the results
Shown in

[Table 2]

Test Example 2 Soybeans were sowed in an upland field and grown for 19 days. 10 parts of Compound A, 2 parts of a mixture of polyoxyethylene alkyl aryl phosphate and polyoxyethylene alkyl aryl ether, and 25 parts of water are mixed, and wet mixed until the average particle size becomes 5 micrometers or less. A thickener comprising xanthan gum and smectite clay and 11 parts of an antifreezing agent (propylene glycol) were added to the pulverized liquid obtained by pulverization, and a suspension of compound A was prepared with water to make the total amount 100 parts. The above imazethapyr preparation And a mixture of the compound A suspension and the imazethapyr preparation are each diluted with water to obtain a tractor.
Was sprayed evenly from above the soybean and the P. aeruginosa generated in the field with the sprayer installed in the field. Seven days after the treatment, the herbicidal efficacy and the safety to soybean were investigated. Table 3 shows the results.

[Table 3]

Test Example 3 Field soil was filled in a plastic pot having an area of 26.5 × 19 cm ² and a depth of 7 cm, soybean, Aquino nokorogosa,
The crabgrass and rice millet were sowed and grown in a greenhouse for 23 days. An emulsion of compound A obtained by thoroughly mixing 10 parts of compound A, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone, an imazaquin preparation (trade name: Scepter: American A predetermined amount of each of the mixture of the compound A and the imazaquin preparation was diluted with water, and the mixture was uniformly sprayed from above the plant with a small sprayer. The plants were grown in a greenhouse for 5 days after the treatment, and their herbicidal efficacy and safety against soybean were investigated. Table 4 shows the results.

[Table 4]

[0022]

EFFECT OF THE INVENTION By using the composition of the present invention, a wide range of weeds in a soybean field, particularly in a soybean field, can be selectively removed.

Claims (4)

[Claims] (1) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenoxyacetic acid ester derivative and (±) -2
-[4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1H-imidazol-2-yl] -5-ethyl-3-pyridinecarboxylic acid or a salt thereof, ±) -2- [4,5-dihydro-4-methyl-4
-(1-Methylethyl) -5-oxo-1H-imidazole-2-yl] -3-quinolinecarboxylic acid or a salt thereof and 2- (4-isopropyl-4-methyl-5-oxo-2-imidazoline -2-yl) -5- (methoxymethyl) nicotinic acid or one selected from the group consisting of salts thereof as an active ingredient. 2. The herbicidal composition according to claim 1, for controlling weeds in a soybean field. (3) 2-chloro-4-fluoro-5- (4-methyl-5-trifluoromethyl-3-pyridazinone-2)
-Yl) phenoxyacetic acid ester derivative and (±) -2
-[4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1H-imidazol-2-yl] -5-ethyl-3-pyridinecarboxylic acid or a salt thereof, ±) -2- [4,5-dihydro-4-methyl-4
-(1-Methylethyl) -5-oxo-1H-imidazole-2-yl] -3-quinolinecarboxylic acid or a salt thereof and 2- (4-isopropyl-4-methyl-5-oxo-2-imidazoline -2-yl) -5- (methoxymethyl) nicotinic acid or a salt thereof, and a herbicide containing as an active ingredient a foliage treatment on weeds. 4. A method for treating weeds in a soybean field.
The method for weeding described in 1.